25491-28-5Relevant articles and documents
Structural verification via convergent total synthesis of dipeptide–lipids isolated from Porphyromonas gingivalis
Dietz, Christopher,Hart, Theresa K.,Nemati, Reza,Yao, Xudong,Nichols, Frank C.,Smith, Michael B.
, p. 7557 - 7569 (2016/11/11)
A periodontal pathogen, Porphyromonas gingivalis, produces two serine dipeptide lipid classes that we labeled lipid 654 and lipid 430, and both contain L-serine as the terminal amino acid. The lipid 654 and lipid 430 classes are each comprised of three species with differing fatty acid substitutions, but the most abundant species demonstrate unit masses of either 654 or 430, respectively. Recently we observed that the lipid 654 can be hydrolyzed by specific lipases to lipid 430. However, a substantial percentage of the naturally occurring lipid 654 cannot be enzymatically hydrolyzed to lipid 430. The observed partial hydrolysis could be due to the presence of a mixture of stereoisomers. Testing this theory requires structural verification of our so-called 654 and 430 by total synthesis. We present herein details of the convergent synthesis of lipids 430 and 654, which confirm the proposed structure of P. gingivalis lipid 654 to be (3R and 3S)-L-serine-2. The bis(fatty acid) (3R)-L-serine-2 was prepared as well as the synthetic precursor, serine dipeptide mono-fatty acid (3R)-L-serine-1, which is the structure of lipid 430. We also synthesized the (3S)-L-serine-2 diastereomer as well as (3S)-L-serine-1. Using these synthetic standards, we confirmed that PLA2-mediated hydrolysis of lipid 654 is enantioselective in that only the (3R)-L-serine-2, but not (3S)-L-serine 2 is enzymatically hydrolyzed.
Structural confirmation of the dihydrosphinganine and fatty acid constituents of the dental pathogen Porphyromonas gingivalis
Mun, JiYoung,Onorato, Amber,Nichols, Frank C.,Morton, Martha D.,Saleh, Abdullah I.,Welzel, Morgan,Smith, Michael B.
, p. 3826 - 3833 (2008/10/09)
Porphyromonas gingivalis, a recognized periodontal pathogen, is a source of sphinganine bases, fatty acids, free ceramides as well as complex lipids that potentiate interleukin-1b-mediated secretory responses in gingival fibroblasts. The purpose of this study is the structural verification of the sphinganine bases and fatty acids that had been proposed as major components of the complex lipids found in P. gingivalis. The putative C17, C18, and C19 sphinganine bases were prepared from Garner's aldehyde (1) or from a protected serine Weinreb's amide (2). We confirmed that isobranched sphinganine bases are the major structural feature of the ceramides observed from P. gingivalis. We also prepared a C17 unsaturated fatty acid, along with an isobranched C17 3-hydroxy fatty acid, and determined that the major component of the active lipids was the latter. The Royal Society of Chemistry 2007.
Synthesis of sphingosine relatives. Part 22. Synthesis of sulfobacin A, B and flavocristamide A, new sulfonolipids isolated from Chryseobacterium sp.
Takikawa, Hirosato,Nozawa, Dai,Kayo, Akihiro,Muto, Shin-Etsu,Mori, Kenji
, p. 2467 - 2477 (2007/10/03)
Sulfobacin A (1), B (2), and flavocristamide A (3), new sulfonolipids isolated from Chryseobacterium sp. were synthesized stereoselectively by starting from L-cysteine.
